CORE COURSE (HONOURS) IN CHEMISTRY

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SEMESTER-I
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CHEMISTRY -C I: ORGANIC CHEMISTRY-I (PAPER-1A) (O-

1A)
(Credits: Theory-04, Practicals-02)
Theory: 40 Lectures
Basics of Organic Chemistry
Bonding and Physical Properties (18 Lectures)

Valence Bond Theory: concept of hybridisation, shapes of molecules, resonance (including

hyperconjugation); calculation of formal charges and double bond equivalent (DBE); orbital
pictures of bonding (sp3, sp2, sp: C-C, C-N & C-O systems and s-cis and s-trans geometry for
suitable cases).
Electronic displacements: inductive effect, field effect, mesomeric effect, resonance energy;
bond polarization and bond polarizability; electromeric effect; steric effect, steric inhibition
of resonance.
MO theory: qualitative idea about molecular orbitals, bonding and antibonding interactions,
idea about σ, σ*, π, π *, n – MOs; concept of HOMO, LUMO and SOMO; sketch and energy
levels of π MOs of i) acyclic p orbital system (C=C, conjugated diene, triene, allyl and
pentadienyl systems) ii) cyclic p orbital system (neutral systems: [4], [6] annulenes; charged
systems: 3-,4-,5-membered ring systems); Hückel’s rules for aromaticity up to [8] annulene
(including mononuclear heterocyclic compounds up to 6-membered ring); concept of
antiaromaticity and homoaromaticity; non-aromatic molecules; Frost diagram (qualitative
drawing).
Physical properties: influence of hybridization on bond properties: bond dissociation energy
(BDE) and bond energy; bond distances, bond angles; concept of bond angle strain; melting
point/boiling point and solubility of common organic compounds in terms of covalent & non-
covalent intermolecular forces; polarity of molecules and dipole moments; relative stabilities
of isomeric hydrocarbons in terms of heat of hydrogenation and heat of combustion data.
General Treatment of Reaction Mechanism I (02 Lectures)
Mechanistic classification: ionic, radical and pericyclic (definition and example);
reaction type: addition, elimination and substitution reactions (definition and example);
nature of bond cleavage and bond formation: homolytic and heterolytic bond fission,
homogenic and heterogenic bond formation; curly arrow rules in representation of
mechanistic steps; reagent type: electrophiles and nucleophiles (elementary idea).

CHEMISTRY -C I: ORGANIC CHEMISTRY-I (PAPER-2B) (O-

1B)
Stereochemistry I (17 Lectures)
Bonding geometries of carbon compounds and representation of molecules: tetrahedral
nature of carbon and concept of asymmetry; Fischer, sawhorse, flying wedge and Newman
projection formulae and their inter translations.
Concept of chirality and symmetry: symmetry elements, molecular chirality and centre of
chirality; asymmetric and dissymmetric molecules; enantiomers and diastereomers; concept
of stereogenicity, chirotopicity and pseudoasymmetry; chiral centres and number of
stereoisomerism: systems involving 1/2/3-chiral centre(s) (AA, AB, ABA and ABC types).
Relative and absolute configuration: D/L and R/S descriptors; erythro/threo and meso
nomenclature of compounds; syn/anti nomenclatures for aldols; E/Z descriptors for C=C,
conjugated diene, triene, C=N and N=N systems; combination of R/S- and E/ Z- isomerisms.
Optical activity of chiral compounds: optical rotation, specific rotation and molar rotation;
racemic compounds, racemisation (through cationic, anionic, radical intermediates and
through reversible formation of stable achiral intermediates); resolution of acids, bases and
alcohols via diastereomeric salt formation; optical purity and enantiomeric excess;
invertomerism of chiral trialkylamines.
General Treatment of Reaction Mechanism II (03 Lectures)
Reactive intermediates: carbocations (carbenium and carbonium ions), non-classical
cabocations, carbanions, carbon radicals, carbenes: generation and stability, structure using
orbital picture and electrophilic/nucleophilic behavior of reactive intermediates (elementary
idea).

Reference Books
1. Finar, I. L. Organic Chemistry (Volume 1), Dorling Kindersley (India) Pvt. Ltd.
(Pearson Education).
2. Morrison, R. N. & Boyd, R. N. Organic Chemistry, Dorling Kindersley (India) Pvt. Ltd.
(Pearson Education).
3. Sykes, P. A guidebook to Mechanism in Organic Chemistry, Pearson Education, 2003.
4. Carey, F. A., Guiliano, R. M. Organic Chemistry, Eighth edition, McGraw Hill Education,
2012.
5. Eliel, E. L. & Wilen, S. H. Stereochemistry of Organic Compounds, Wiley: London, 1994.
6. Nasipuri, D. Stereochemistry of Organic Compounds, Wiley Eastern Limited.
7. Clayden, J., Greeves, N. & Warren, S. Organic Chemistry, Second edition, Oxford
University Press, 2012.
8. Keeler, J., Wothers, P. Chemical Structure and Reactivity – An Integrated approach,
Oxford University Press.
9. Smith, J. G. Organic Chemistry, Tata McGraw-Hill Publishing Company Limited.
10.Fleming, I. Molecular Orbitals and Organic Chemical Reactions, Reference/Student
Edition, Wiley, 2009.
11. James, J., Peach, J. M. Stereochemistry at a Glance, Blackwell Publishing, 2003.
12. Robinson, M. J. T., Stereochemistry, Oxford Chemistry Primer, Oxford University Press,
2005.
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CHEMISTRY LAB-C I LAB

(60 Lectures)

1. Separation based upon solubility, by using common laboratory reagents like water (cold,
hot), dil. HCl, dil. NaOH, dil. NaHCO3, etc., of components of a binary solid mixture;
purification of any one of the separated components by crystallization and determination of
its melting point. The composition of the mixture should be of the following types [ANY
THREE]: p-Nitrobenzoic acid/p-Aminobenzoic acid; p-Nitrotolune/p-Anisidine; benzoic
acid/naphthalene; urea/phenyl benzoate; p-toluidine/benzophenone; p-chlorobenzoic acid/
benzophenone, Benzoic acid/Anthracene; Glucose/Biphenyl; Benzoic acid/Benzophenone;
Urea/Benzophenone. Use of pH paper is recommended.

2. Determination of boiling point of common organic liquid compounds [ANY FIVE] n-

butyl alcohol, cyclohexanol, ethyl methyl ketone, cyclohexanone, acetylacetone, isobutyl
methyl ketone, isobutyl alcohol, acetonitrile, benzaldehyde and acetophenone. [Boiling points
of the chosen organic compounds should preferably be within 1800C].

3. Identification of a Pure Organic Compound

Solid compounds: oxalic acid, tartaric acid, citric acid, succinic acid, resorcinol,
urea, glucose, cane sugar, benzoic acid and salicylic acid

Liquid Compounds: formic acid, acetic acid, methyl alcohol, ethyl alcohol,
acetone, aniline, dimethylaniline, benzaldehyde, chloroform and nitrobenzene

Reference Books

1. Bhattacharyya, R. C, A Manual of Practical Chemistry.

2. Vogel, A. I. Elementary Practical Organic Chemistry, Part 2: Qualitative Organic
Analysis, CBS Publishers and Distributors.
3. Mann, F.G. & Saunders, B.C. Practical Organic Chemistry, Pearson Education (2009).
4. Furniss, B.S., Hannaford, A.J., Smith, P.W.G., Tatchell, A.R. Practical Organic
Chemistry,5th Ed., Pearson (2012).
5. Dutta, S, B. Sc. Honours Practical Chemistry, Bharati Book Stall.

CHEMISTRY -C IV: ORGANIC CHEMISTRY-II(PAPER-3) (O-2)

(Credits: Theory-04, Practicals-02)
Theory: 60 Lectures
Stereochemistry II (20 Lectures)
Chirality arising out of stereoaxis: stereoisomerism of substituted cumulenes with even and
odd number of double bonds; chiral axis in allenes, spiro compounds, alkylidenecycloalkanes
and biphenyls; related configurational descriptors (Ra/Sa); atropisomerism; racemisation of
chiral biphenyls.
Concept of prostereoisomerism: prostereogenic centre; concept of (pro)n-chirality: topicity of
ligands and faces (elementary idea); pro-R/pro-S, pro-E/pro-Z and Re/Si descriptors; pro-r
and pro-s descriptors of ligands on propseudoasymmetric centre.
Conformation: conformational nomenclature: eclipsed, staggered, gauche, syn and anti;
dihedral angle, torsion angle; Klyne-Prelog terminology; P/M descriptors; energy barrier of
rotation, concept of torsional and steric strains; relative stability of conformers on the basis of
steric effect, dipole-dipole interaction and H-bonding; butane gauche interaction;
conformational analysis of ethane, propane, n-butane, 2-methylbutane and 2,3-
dimethylbutane; haloalkane, 1,2-dihaloalkanes and 1,2-diols (up to four carbons); 1,2-
halohydrin; conformation of conjugated systems (s-cis and s-trans).
General Treatment of Reaction Mechanism III (20 lectures)
Reaction thermodynamics: free energy and equilibrium, enthalpy and entropy factor,
calculation of enthalpy change via BDE, intermolecular & intramolecular reactions.
Concept of organic acids and bases: effect of structure, substituent and solvent on acidity and
basicity; proton sponge; comparison between nucleophilicity and basicity; application of
thermodynamic principles in acid-base equilibria.
Tautomerism: prototropy (keto-enol, nitro - aci-nitro, nitroso-oximino, diazo-amino and
enamine-imine systems); valence tautomerism and ring-chain tautomerism; composition of
the equilibrium in different systems (simple carbonyl; 1,2- and 1,3-dicarbonyl systems,
phenols and related systems), factors affecting keto-enol tautomerism; application of
thermodynamic principles in tautomeric equilibria.
Reaction kinetics: rate constant and free energy of activation; concept of order and
molecularity; free energy profiles for one-step, two-step and three-step reactions; catalyzed
reactions: electrophilic and nucleophilic catalysis; kinetic control and thermodynamic control
of reactions; isotope effect: primary and β-secondary kinetic isotopic effect (kH /kD); principle
of microscopic reversibility; Hammond’s postulate.
Substitution and Elimination Reactions (20 Lectures)
Free-radical substitution reaction: halogentaion of alkanes, mechanism (with evidence) and
stereochemical features; reactivity-selectivity principle in the light of Hammond’s postulate.
Nucleophilic substitution reactions: substitution at sp3 centre [systems: alkyl halides, allyl
halides, benzyl halides, alcohols, ethers, epoxides, -halocarbonyls]: mechanisms (with
evidence), relative rates & stereochemical features: SN1, SN2, SN2', SN1' (allylic
rearrangement) and SNi; effects of solvent, substrate structure, leaving group and nucleophiles
(including ambident nucleophiles, cyanide & nitrite); substitutions involving NGP (with
hetero atoms and aryl groups); role of crown ethers and phase transfer catalysts.
Elimination reactions: E1, E2, E1cB and Ei (pyrolytic syn eliminations); formation of
alkenes and alkynes; mechanisms (with evidence), reactivity, regioselectivity
(Saytzeff/Hofmann) and stereoselectivity; comparison between substitution and elimination.
Reference Books:
1. Finar, I. L. Organic Chemistry (Volume 1), Dorling Kindersley (India) Pvt. Ltd.
(Pearson Education).
2. Morrison, R. N. & Boyd, R. N. Organic Chemistry, Dorling Kindersley (India) Pvt. Ltd.
(Pearson Education).
3. Sykes, P. A guidebook to Mechanism in Organic Chemistry, Pearson Education, 2003.
4. Carey, F. A., Guiliano, R. M. Organic Chemistry, Eighth edition, McGraw Hill Education,
2012.
5. Eliel, E. L. & Wilen, S. H. Stereochemistry of Organic Compounds, Wiley: London, 1994.
6. Nasipuri, D. Stereochemistry of Organic Compounds, Wiley Eastern Limited.
7. Clayden, J., Greeves, N. & Warren, S. Organic Chemistry, Second edition, Oxford
University Press, 2012.
8. Keeler, J., Wothers, P. Chemical Structure and Reactivity – An Integrated approach,
Oxford University Press.
9. Smith, J. G. Organic Chemistry, Tata McGraw-Hill Publishing Company Limited.
10.Fleming, I. Molecular Orbitals and Organic Chemical Reactions, Reference/Student
Edition, Wiley, 2009.
11. James, J., Peach, J. M. Stereochemistry at a Glance, Blackwell Publishing, 2003.
12. Robinson, M. J. T., Stereochemistry, Oxford Chemistry Primer, Oxford University Press,
2005.
13. Maskill, H., Mechanisms of Organic Reactions, Oxford Chemistry Primer, Oxford
University Press.

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CHEMISTRY LAB-C IV LAB
60 Lectures
Organic Preparations
A. The following reactions (any eight) are to be performed, noting the yield of the crude
product:
1. Nitration of aromatic compounds
2. Condensation reactions
3. Hydrolysis of amides/imides/esters
4. Acetylation of phenols/aromatic amines
5. Brine mediated benzoylation of amines/amino acids.
6. Side chain oxidation of aromatic compounds
7. Diazo coupling reactions of aromatic amines
8. Bromination of anilides using green approach (Bromate-Bromide method)
9. Redox reaction including solid-phase method
10. Green ‘multi-component-coupling’ reaction
11. Selective reduction of m-dinitrobenzene to m-nitroaniline

Students must also calculate percentage yield, based upon isolated yield (crude) and
theoretical yield.

B. Purification of the crude product is to be made by crystallisation from water/alcohol,

crystallization after charcoal treatment, or sublimation, whichever is applicable.

C. Melting point of the purified product is to be noted.

Reference Books

1. Vogel, A. I. Elementary Practical Organic Chemistry, Part 1: Small scale

Preparations, CBS Publishers and Distributors.

2. Mann, F.G. & Saunders, B.C. Practical Organic Chemistry, Pearson Education
(2009).
3. Furniss, B.S., Hannaford, A.J., Smith, P.W.G. & Tatchell, A.R. Practical Organic
Chemistry, 5th Ed. Pearson (2012).
4. Ahluwalia, V.K. & Aggarwal, R. Comprehensive Practical Organic Chemistry:
Preparation and Quantitative Analysis, University Press (2000).
5. Practical Workbook Chemistry (Honours), UGBS, Chemistry, University of Calcutta,
2015.

CHEMISTRY - C VII: ORGANIC CHEMISTRY-III (PAPER-7)

(O-3)
(Credits: Theory-04, Practicals-02)
Theory: 60 Lectures
Chemistry of alkenes and alkynes (15 Lectures)
Addition to C=C: mechanism (with evidence wherever applicable), reactivity,
regioselectivity (Markownikoff and anti-Markownikoff additions) and stereoselectivity;
reactions: hydrogenation, halogenation, hydrohalogenation, hydration, oxymercuration-
demercuration, hydroboration-oxidation, epoxidation, syn and anti-hydroxylation, ozonolysis,
addition of singlet and triplet carbenes; Simmons-Smith cyclopropanation reaction;
electrophilic addition to diene (conjugated dienes and allene); radical addition: HBr addition;
mechanism of allylic and benzylic bromination in competition with brominations across
C=C; use of NBS; Birch reduction of benzenoid aromatics; interconversion of E- and Z-
alkenes; contra-thermodynamic isomerization of internal alkenes.
Addition to C≡C (in comparison to C=C): mechanism, reactivity, regioselectivity
(Markownikoff and anti-Markownikoff addition) and stereoselectivity; reactions:
hydrogenation, halogenations, hydrohalogenation, hydration, oxymercuration-demercuration,
hydroboration-oxidation, dissolving metal reduction of alkynes (Birch); reactions of terminal
alkynes by exploring its acidity; interconversion of terminal and non-terminal alkynes.
Aromatic Substitution (10 Lectures)
Electrophilic aromatic substitution: mechanisms and evidences in favour of it; orientation
and reactivity; reactions: nitration, nitrosation, sulfonation, halogenation, Friedel-Crafts
reaction; one-carbon electrophiles (reactions: chloromethylation, Gatterman-Koch,
Gatterman, Houben-Hoesch, Vilsmeier-Haack, Reimer-Tiemann, Kolbe-Schmitt); Ipso
substitituion.
Nucleophilic aromatic substitution: addition-elimination mechanism and evidences in favour
of it; SN1 mechanism; cine substitution (benzyne mechanism), structure of benzyne.
Carbonyl and Related Compounds (30 Lectures)
Addition to C=O: structure, reactivity and preparation of carbonyl compounds; mechanism
(with evidence), reactivity, equilibrium and kinetic control; formation of hydrates,
cyanohydrins and bisulphite adduct; nucleophilic addition-elimination reactions with
alcohols, thiols and nitrogen- based nucleophiles; reactions: benzoin condensation,
Cannizzaro and Tischenko reactions, reactions with ylides: Wittig and Corey-Chaykovsky
reaction; Rupe rearrangement, oxidations and reductions: Clemmensen, Wolff-Kishner,
LiAlH4, NaBH4, MPV, Oppenauer, Bouveault-Blanc, acyloin condensation; oxidation of
alcohols with PDC and PCC; periodic acid and lead tetraacetate oxidation of 1,2-diols.
Exploitation of acidity of α-H of C=O: formation of enols and enolates; kinetic and
thermodynamic enolates; reactions (mechanism with evidence): halogenation of carbonyl
compounds under acidic and basic conditions, Hell-Volhard-Zelinsky (H. V. Z.) reaction,
nitrosation, SeO2 (Riley) oxidation; condensations (mechanism with evidence): Aldol,
Tollens’, Knoevenagel, Claisen-Schmidt, Claisen ester including Dieckmann, Stobbe;
Mannich reaction, Perkin reaction, Favorskii rearrangement; alkylation of active methylene
compounds; preparation and synthetic applications of diethyl malonate and ethyl
acetoacetate; specific enol equivalents (lithium enolates, enamines and silyl enol ethers) in
connection with alkylation, acylation and aldol type reaction.
Nucleophilic addition to α,β-unsaturated carbonyl system: general principle and mechanism
(with evidence); direct and conjugate addition, addition of enolates (Michael reaction), Stetter
reaction, Robinson annulation.
Substitution at sp2 carbon (C=O system): mechanism (with evidence): BAC2, AAC2, AAC1,
AAL1 (in connection to acid and ester); acid derivatives: amides, anhydrides & acyl halides
(formation and hydrolysis including comparison).
Organometallics (5 Lectures)
Grignard reagent; Organolithiums; Gilman cuprates: preparation and reactions (mechanism
with evidence); addition of Grignard and organolithium to carbonyl compounds; substitution
on -COX; directed ortho metalation of arenes using organolithiums, conjugate addition by
Gilman cuprates; Corey-House synthesis; abnormal behaviour of Grignard reagents;
comparison of reactivity among Grignard, organolithiums and organocopper reagents;
Reformatsky reaction; Blaise reaction; concept of umpolung.
Reference Books
1. Finar, I. L. Organic Chemistry (Volume 1), Dorling Kindersley (India) Pvt. Ltd.
(Pearson Education).
2. Morrison, R. N. & Boyd, R. N. Organic Chemistry, Dorling Kindersley (India) Pvt. Ltd.
(Pearson Education).
3. Sykes, P. A guidebook to Mechanism in Organic Chemistry, Pearson Education, 2003.
4. Carey, F. A., Guiliano, R. M. Organic Chemistry, Eighth edition, McGraw Hill Education,
2012.
5. Loudon, G. M. Organic Chemistry, Fourth edition, Oxford University Press, 2008.
6. Norman, R.O. C., Coxon, J. M. Principles of Organic Synthesis, Third Edition, Nelson
Thornes, 2003.
7. Clayden, J., Greeves, N. & Warren, S. Organic Chemistry, Second edition, Oxford
University Press, 2012.
8. Graham Solomons, T.W., Fryhle, C. B. Organic Chemistry, John Wiley & Sons, Inc.
9. Smith, J. G. Organic Chemistry, Tata McGraw-Hill Publishing Company Limited.
10. March, J. Advanced Organic Chemistry, Fourth edition, Wiley.
11. Jenkins, P. R., Organometallic Reagents in Synthesis, Oxford Chemistry Primer, Oxford
University Press.
12. Ward, R. S., Bifunctional Compounds, Oxford Chemistry Primer, Oxford University
Press.

Core Course-VII (LAB)

(60 Lecturers)
Experiment: Qualitative Analysis of Single Solid Organic Compounds
1. Detection of special elements (N, S, Cl, Br) by Lassaigne’s test
2. Solubility and classification (solvents: H2O, 5% HCl, 5% NaOH and 5% NaHCO3)
3. Detection of the following functional groups by systematic chemical tests: aromatic amino
(-NH2), aromatic nitro (-NO2), amido (-CONH2, including imide), phenolic –OH, carboxylic
acid (-COOH), carbonyl (no distinction between -CHO and >C=O needed); only one test for
each functional group is to be reported.
4. Melting point of the given compound
5. Preparation, purification and melting point determination of a crystalline derivative of the
given compound.
6. Identification of the compound through literature survey.
Each student, during laboratory session, is required to carry out qualitative chemical tests for
all the special elements and the functional groups with relevant derivatisation in known and
unknown (at least six) organic compounds.

Reference Books

1. Vogel, A. I. Elementary Practical Organic Chemistry, Part 2: Qualitative

Organic Analysis, CBS Publishers and Distributors.
2. Mann, F.G. & Saunders, B.C. Practical Organic Chemistry, Pearson Education (2009).
3. Furniss, B.S., Hannaford, A.J., Smith, P.W.G., Tatchell, A.R. Practical Organic
Chemistry, 5th Ed., Pearson (2012).
4. Clarke, H. T., A Handbook of Organic Analysis (Qualitative and Quantitative), Fourth
Edition, CBS Publishers and Distributors (2007). 5. Practical Workbook Chemistry
(Honours), UGBS, Chemistry, University of Calcutta, 2015.
CHEMISTRY -C X: ORGANIC CHEMISTRY-IV(PAPER-8) (O-4)
(Credits: Theory-04, Practicals-02)
Theory: 60 Lectures

Nitrogen compounds (12 Lectures)

Amines: Aliphatic & Aromatic: preparation, separation (Hinsberg’s method) and

identification of primary, secondary and tertiary amines; reaction (with mechanism):
Eschweiler–Clarke methylation, diazo coupling reaction, formation and reactions of
phenylenediamines, diazomethane and diazoacetic ester.

Nitro compounds (aliphatic and aromatic): preparation and reaction (with mechanism):
reduction under different conditions; Nef carbonyl synthesis, Henry reaction and conjugate
addition of nitroalkane anion.

Alkylnitrile and isonitrile: preparation and reaction (with mechanism): Thorpe nitrile
condensation, von Richter reaction.

Diazonium salts and their related compounds: reactions (with mechanism) involving
replacement of diazo group; reactions: Gomberg, Meerwein, Japp-Klingermann.

Rearrangements (14 Lectures)

Mechanism with evidence and stereochemical features for the following:
Rearrangement to electron-deficient carbon: Wagner-Meerwein rearrangement, pinacol
rearrangement, dienone-phenol; Wolff rearrangement in Arndt-Eistert synthesis, benzil-
benzilic acid rearrangement, Demjanov rearrangement, Tiffeneau–Demjanov rearrangement.
Rearrangement to electron-deficient nitrogen: rearrangements: Hofmann, Curtius, Lossen,
Schmidt and Beckmann.
Rearrangement to electron-deficient oxygen: Baeyer-Villiger oxidation, cumene
hydroperoxide-phenol rearrangement and Dakin reaction.
Aromatic rearrangements: Migration from oxygen to ring carbon: Fries rearrangement and
Claisen rearrangement.
Migration from nitrogen to ring carbon: Hofmann-Martius rearrangement, Sommelet Hauser
rearrangement, Fischer-Hepp rearrangement, N-azo to C-azo rearrangement, Bamberger
rearrangement, Orton rearrangement and benzidine rearrangement.
The Logic of Organic Synthesis (14 Lectures)
Retrosynthetic analysis: disconnections; synthons, donor and acceptor synthons; natural
reactivity and umpolung; latent polarity in bifunctional compounds: illogical electrophiles
and nucleophiles; synthetic equivalents; functional group interconversion and addition (FGI
and FGA); C-C disconnections and synthesis: one-group and two-group (1,2- to 1,5-
dioxygenated compounds), reconnection (1,6-dicarbonyl); protection-deprotection strategy
(alcohol, amine, carbonyl, acid).
Strategy of ring synthesis: thermodynamic and kinetic factors; synthesis of large rings,
application of high dilution technique.
Asymmetric synthesis: stereoselective and stereospecific reactions; diastereoselectivity and
enantioselectivity (only definition); diastereoselectivity: addition of nucleophiles to C=O
adjacent to a stereogenic centre: Felkin-Anh model.
Organic Spectroscopy (20 Lectures)
UV Spectroscopy: introduction; types of electronic transitions, end absorption; transition
dipole moment and allowed/forbidden transitions; chromophores and auxochromes;
Bathochromic and Hypsochromic shifts; intensity of absorptions (Hyper-/Hypochromic
effects); application of Woodward’s Rules for calculation of λmax for the following systems:
conjugated diene, α,β-unsaturated aldehydes and ketones (alicyclic, homoannular and
heteroannular); extended conjugated systems (dienes, aldehydes and ketones); relative
positions of λmax considering conjugative effect, steric effect, solvent effect, effect of pH;
effective chromophore concentration: keto-enol systems; benzenoid transitions.
IR Spectroscopy: introduction; modes of molecular vibrations (fundamental and non-
fundamental); IR active molecules; application of Hooke’s law, force constant; fingerprint
region and its significance; effect of deuteration; overtone bands; vibrational coupling in IR;
characteristic and diagnostic stretching frequencies of C-H, N-H, O-H, C-O, C-N, C-X, C=C
(including skeletal vibrations of aromatic compounds), C=O, C=N, N=O, C≡C, C≡N;
characteristic/diagnostic bending vibrations are included; factors affecting stretching
frequencies: effect of conjugation, electronic effects, mass effect, bond multiplicity, ring-size,
solvent effect, H-bonding on IR absorptions; application in functional group analysis.
NMR Spectroscopy: introduction; nuclear spin; NMR active molecules; basic principles of
Proton Magnetic Resonance; choice of solvent and internal standard; equivalent and non-
equivalent protons; chemical shift and factors influencing it; ring current effect; significance
of the terms: up-/downfield, shielded and deshielded protons; spin coupling and coupling
constant (1st order spectra); relative intensities of first-order multiplets: Pascal’s triangle;
chemical and magnetic equivalence in NMR ; anisotropic effects in alkene, alkyne, aldehydes
and aromatics; NMR peak area, integration; relative peak positions with coupling patterns of
common organic compounds (both aliphatic and benzenoid-aromatic); rapid proton
exchange; interpretation of NMR spectra of simple compounds.
Applications of IR, UV and NMR spectroscopy for identification of simple organic
molecules.
Reference Books
1. Finar, I. L. Organic Chemistry (Volume 1), Dorling Kindersley (India) Pvt. Ltd. (Pearson
Education).
2. Finar, I. L. Organic Chemistry (Volume 2: Stereochemistry and the Chemistry
of Natural Products), Dorling Kindersley (India) Pvt. Ltd.(Pearson Education).
3. Norman, R.O. C., Coxon, J. M. Principles of Organic Synthesis, Third Edition, Nelson
Thornes, 2003.
4. Clayden, J., Greeves, N., Warren, S., Organic Chemistry, Second edition, Oxford
University Press 2012.
5. Silverstein, R. M., Bassler, G. C., Morrill, T. C. Spectrometric Identification
of Organic Compounds, John Wiley and Sons, INC, Fifth edition.
6. Kemp, W. Organic Spectroscopy, Palgrave.
7. Pavia, D. L. et al. Introduction to Spectroscopy, 5th Ed. Cengage Learning India Ed.
(2015). 8. Dyer, J. Application of Absorption Spectroscopy of Organic Compounds, PHI
Private Limited
9. March, J. Advanced Organic Chemistry, Fourth edition, Wiley.
10. Harwood, L. M., Polar Rearrangements, Oxford Chemistry Primer, Oxford University
Press.
11. Bailey, Morgan, Organonitrogen Chemistry, Oxford Chemistry Primer, Oxford
University Press.
12. Warren, S. Organic Synthesis the Disconnection Approach, John Wiley and Sons.
13. Warren, S., Designing Organic Synthesis, Wiley India, 2009.
14. Carruthers, W. Modern methods of Organic Synthesis, Cambridge University Press.
15. Willis, C. A., Wills, M., Organic Synthesis, Oxford Chemistry Primer, Oxford University
Press
Core Course-IX (LAB)
(60 Lectures)
Quantitative Estimations:
Each student is required to perform all the experiments [ Any FIVE will be set in the
examination]
1. Estimation of glycine by Sörensen’s formol method
2. Estimation of glucose by titration using Fehling’s solution
3. Estimation of sucrose by titration using Fehling’s solution
4. Estimation of aromatic amine (aniline) by bromination (Bromate-Bromide) method
5. Estimation of acetic acid in commercial vinegar
6. Estimation of urea (hypobromite method)
7. Estimation of saponification value of oil/fat/ester

Reference Books
1. Arthur, I. Vogel, Quantitative Organic Analysis, Pearson
2. Practical Workbook Chemistry (Honours), UGBS, Chemistry, University of Calcutta, 2015

CHEMISTRY - C XII: ORGANIC CHEMISTRY - V(PAPER-12)

(O-5)
(Credits: Theory-04, Practicals-02)
Theory: 60 Lectures

Carbocyles and Heterocycles (16 lectures)

Polynuclear hydrocarbons and their derivatives: synthetic methods include Haworth,
Bardhan-Sengupta, Bogert-Cook and other useful syntheses (with mechanistic details);
fixation of double bonds and Fries rule; reactions (with mechanism) of naphthalene,
anthracene and phenanthrene and their derivatives.
Heterocyclic compounds: Biological importance of heterocycles referred in the syllabus; 5-
and 6-membered rings with one heteroatom; reactivity, orientation and important reactions
(with mechanism) of furan, pyrrole, thiophene and pyridine; synthesis (including
retrosynthetic approach and mechanistic details): pyrrole: Knorr synthesis, Paal-Knorr
synthesis, Hantzsch; furan: Paal-Knorr synthesis, Feist-Benary synthesis and its variation;
thiophenes: Paal-Knorr synthesis, Hinsberg synthesis; pyridine: Hantzsch synthesis; benzo-
fused 5- and 6-membered rings with one heteroatom: reactivity, orientation and important
reactions (with mechanistic details) of indole, quinoline and isoquinoline; synthesis
(including retrosynthetic approach and mechanistic details): indole: Fischer, Madelung and
Reissart; quinoline: Skraup, Doebner – Miller, Friedlander; isoquinoline: Bischler-
Napieralski synthesis.
Cyclic Stereochemistry (10 Lectures)
Alicyclic compounds: concept of I-strain (Baeyer’s strain theory); conformational analysis:
cyclohexane, mono and disubstituted cyclohexane; symmetry properties and optical activity;
topomerisation; ring size and ease of cyclisation; conformation & reactivity in cyclohexane
system: consideration of steric and stereoelectronic requirements; elimination (E2, E1),
nucleophilic substitution (SN1, SN2, SNi, NGP), merged substitution-elimination;
rearrangements; oxidation of cyclohexanol, esterification, saponification, lactonisation,
epoxidation, pyrolytic syn elimination and fragmentation reactions.
Pericyclic reactions (08 Lectures)
Mechanism, stereochemistry, regioselectivity in case of
Electrocyclic reactions: FMO approach involving 4π- and 6π-electrons (thermal and
photochemical) and corresponding cycloreversion reactions.
Cycloaddition reactions: FMO approach, Diels-Alder reaction, photochemical [2+2]
cycloadditions.
Sigmatropic reactions: FMO approach, sigmatropic shifts and their order; [1,3] and [1,5] H
shifts and [3,3] shifts with reference to Claisen and Cope rearrangements.
Carbohydrates (14 Lectures)
Monosaccharides: Aldoses up to 6 carbons; structure of D-glucose & D-fructose
(configuration & conformation); ring structure of monosaccharides (furanose and pyranose
forms): Haworth representations and non-planar conformations; anomeric effect (including
stereoelectronic explanation); mutarotation; epimerization; reactions (mechanisms in relevant
cases): Fischer glycosidation, osazone formation, bromine-water oxidation, HNO3 oxidation,
selective oxidation of terminal –CH2OH of aldoses, reduction to alditols, Lobry de Bruyn-van
Ekenstein rearrangement; stepping–up (Kiliani-Fischer method) and stepping–down (Ruff’s
& Wohl’s methods) of aldoses; end-group-interchange of aldoses; acetonide (isopropylidene
and benzylidene protections; ring size determination; Fischer’s proof of configuration of (+)-
glucose.
Disaccharides: Glycosidic linkages, concept of glycosidic bond formation by glycosyl donor-
acceptor, structure of sucrose, inversion of cane sugar.
Biomolecules (12 Lectures)
Amino acids: synthesis with mechanistic details: Strecker, Gabriel; acetamido malonic ester,
azlactone, Bücherer hydantoin synthesis, synthesis involving diketopiperizine, isoelectric
point, zwitterions; electrophoresis, reaction (with mechanism): ninhydrin reaction, Dakin-
West reaction; resolution of racemic amino acids.
Peptides: peptide linkage and its geometry; syntheses (with mechanistic details) of peptides
using N-protection & C-protection, solid-phase (Merrifield) synthesis; peptide sequence: C-
terminal and N-terminal unit determination (Edman, Sanger and ‘dansyl’ methods); partial
hydrolysis; specific cleavage of peptides; use of CNBr.
Nucleic acids: pyrimidine and purine bases (only structure & nomenclature); nucleosides and
nucleotides corresponding to DNA and RNA; mechanism for acid catalysed hydrolysis of
nucleosides (both pyrimidine and purine types); comparison of alkaline hydrolysis of DNA
and RNA; elementary idea of double helical structure of DNA (Watson-Crick model);
complimentary base–pairing in DNA.
Reference Books
1. Clayden, J., Greeves, N., Warren, S. Organic Chemistry, Second edition, Oxford
University Press 2012.
2. Eliel, E. L. & Wilen, S. H. Stereochemistry of Organic Compounds, Wiley: London.
3. Nasipuri, D. Stereochemistry of Organic Compounds, Wiley Eastern Limited.
4. Fleming, I. Molecular Orbitals and Organic Chemical reactions, Reference/Student
Edition, Wiley, 2009.
5. Fleming, I. Pericyclic Reactions, Oxford Chemistry Primer, Oxford University Press.
6. Gilchrist, T. L. & Storr, R. C. Organic Reactions and Orbital symmetry, Cambridge
University Press.
7. Finar, I. L. Organic Chemistry (Volume 1), Dorling Kindersley (India) Pvt. Ltd. (Pearson
Education).
8. Finar, I. L. Organic Chemistry (Volume 2: Stereochemistry and the Chemistry
of Natural Products), Dorling Kindersley (India) Pvt. Ltd. (Pearson Education).
9. Morrison, R. T. & Boyd, R. N. Organic Chemistry, Dorling Kindersley (India) Pvt. Ltd.
(Pearson Education).
10. Loudon, G. M. Organic Chemistry, Fourth edition, Oxford University Press.
11. James, J., Peach, J. M. Stereochemistry at a Glance, Blackwell Publishing, 2003.
12. Robinson, M. J. T., Stereochemistry, Oxford Chemistry Primer, Oxford University Press,
2005.
13. Davis, B. G., Fairbanks, A. J., Carbohydrate Chemistry, Oxford Chemistry Primer,
Oxford University Press.
14. Joule, J. A. Mills, K. Heterocyclic Chemistry, Blackwell Science.
15. Acheson, R.M. Introduction to the Chemistry of Heterocyclic compounds, John Wiely &
Sons (1976).
16. Gilchrist, T. L. Heterocyclic Chemistry, 3rd edition, Pearson.
17. Davies, D. T., Heterocyclic Chemistry, Oxford Chemistry Primer, Oxford University
Press

Core Course-XII (LAB)

(60 Lectures)

A. Chromatographic Separations
1. TLC separation of a mixture containing 2/3 amino acids 2. TLC separation of a mixture of
dyes (fluorescein and methylene blue) 3. Column chromatographic separation of mixture of
dyes 4. Paper chromatographic separation of a mixture containing 2/3 amino acids 5. Paper
chromatographic separation of a mixture containing 2/3 sugars
B. Spectroscopic Analysis of Organic Compounds
1. Assignment of labelled peaks in the 1H NMR spectra of the known organic compounds
explaining the relative δ-values and splitting pattern.
2. Assignment of labelled peaks in the IR spectrum of the same compound explaining the
relative frequencies of the absorptions (C-H, O-H, N-H, C-O, C-N, C-X, C=C, C=O, N=O,
C≡C, C≡N stretching frequencies; characteristic bending vibrations are included).
3. The students must record full spectral analysis of at least 15 (fifteen) compounds from the
following list:
(i) 4-Bromoacetanilide (ii) 2-Bromo-4'-methylacetophenone (iii) Vanillin (iv) 2-
Methoxyacetophenone (v) 4-Aminobenzoic acid (vi) Salicylamide (vii) 2-
Hydroxyacetophenone (viii) 1,3-Dinitrobenzene (ix) trans-Cinnamic acid (x) Diethyl
fumarate (xi) 4-Nitrobenzaldehyde (xii) 4-Methylacetanilide (xiii) Mesityl oxide (xiv) 2-
Hydroxybenzaldehyde (xv) 4-Nitroaniline (xvi) 2,3-Dimethylbenzonitrile (xvii) Pent- 1-yn-3-
ol (xviii) 3-Nitrobenzaldehyde (xix) 3-Aminobenzoic acid (xx) Ethyl 3- aminobenzoate (xxi)
Ethyl 4-aminobenzoate (xxii) 3-nitroanisole.

Reference

1. Practical Workbook Chemistry (Honours), UGBS, Chemistry, University of Calcutta, 2015

2. Furniss, B.S.; Hannaford, A.J.; Smith, P.W.G.; Tatchell, A.R. Practical Organic
Chemistry, 5th Ed., Pearson (2012).
3. Mann, F.G. & Saunders, B.C. Practical Organic Chemistry, Pearson Education.

DSE-4: GREEN CHEMISTRY AND CHEMISTRY OF NATURAL

PRODUCTS
(Credits: Theory-04, Practicals-02)
Theory: 60 Lectures
Introduction to Green Chemistry: (04 Lectures)

What is Green Chemistry? Need for Green Chemistry. Goals of Green Chemistry.
Limitations/ Obstacles in the pursuit of the goals of Green Chemistry

Principles of Green Chemistry and Designing a Chemical synthesis: (16 Lectures)

Twelve principles of Green Chemistry with their explanations and examples and special
emphasis on the following:

 Designing a Green Synthesis using these principles; Prevention of Waste/ byproducts;

maximum incorporation of the materials used in the process into the final products ,
Atom Economy, calculation of atom economy of the rearrangement, addition,
substitution and elimination reactions. 
 Prevention/ minimization of hazardous/toxic products reducing toxicity. 

 Green solvents–supercritical fluids, water as a solvent for organic reactions, ionic
 liquids, PEG, solventless processes. 
 Energy requirements for reactions – alternative sources of energy: use of microwaves
 and ultrasonic energy. 
 Use of catalytic reagents (wherever possible) in preference to stoichiometric reagents;
 catalysis and green chemistry. 

Examples of Green Synthesis/ Reactions and some real world cases: (20 lectures)
1. Green Synthesis of the following compounds: adipic acid, catechol, disodium
iminodiacetate (alternative to Strecker synthesis)
2. Microwave assisted reactions in water: Hofmann Elimination, methyl benzoate to benzoic
acid, oxidation of toluene and alcohols; microwave assisted reactions in organic solvents:
Diels-Alder reaction and Decarboxylation reaction
3. Ultrasound assisted reactions: sonochemical Simmons-Smith Reaction (Ultrasonic
alternative to Iodine)
4. Green counterpart of common organic reactions: Aldol, Friedel-Crafts, Michael,
Knoevenagel, Cannizzaro, benzoin condensation and Dieckmann condensation.
5. Rearrangement reactions by green approach: Fries rearrangement, Claisen rearrangement,
Beckmann rearrangement, Baeyer-Villiger oxidation.

Future Trends in Green Chemistry: (12 Lectures)

Oxidation reagents and catalysts; Biomimetic, multifunctional reagents; Combinatorial green
chemistry; Proliferation of solventless reactions. Green chemistry in sustainable
development.

Alkaloids (5 Lectures)
Hoffmann’s exhaustive methylation, Emde’s modification, Structure elucidation Natural
occurrence, General structural features, Isolation and their physiological action. Synthesis of
Hygrine. Medicinal importance of Nicotine, Hygrine, Quinine, Morphine, Cocaine and
Reserpine.

Terpenes (3 Lectures)
Occurrence, classification, isoprene rule; Elucidation of stucture and synthesis of Citral.
Reference Books

 Anastas, P.T. & Warner, J.K.: Green Chemistry - Theory and Practical, Oxford
 University Press (1998). 
 Matlack, A.S. Introduction to Green Chemistry, Marcel Dekker (2001). 
 Cann, M.C. & Connely, M.E. Real-World cases in Green Chemistry, American Chemical
Society, Washington (2000). 
 Ryan, M.A. & Tinnesand, M. Introduction to Green Chemistry, American Chemical
Society, Washington (2002). 
 Lancaster, M. Green Chemistry: An Introductory Text RSC Publishing, 2nd Edition, 2010.
6. Ahluwalia, V. K & Kidwai, M. R. New Trends in Green Chemistry, Anamalaya
Publishers, 2005. 

---------------------------------------------------------------------------------------------------------
PRACTICALS-DSE-4 LAB GREEN CHEMISTRY
(60 Lectures)
THE FOLLOWING ARE THE PRACTICAL EXPERIMENTS TO BE SET IN DSE-4:
(Any SIX of the following list)
1. Acetylation of primary amine (preparation of acetanilide).
2. [4+2] Cycloaddition reaction (Diels-Alder reaction between furan and maleic
anhydride).
3. Preparation of biodiesel from vegetable/waste cooking oil.
4. Photoreduction of benzophenone to benzopinacol in the presence of sunlight.
5. Pinacol-pinacolone rearrangement reaction (preparation of benzopinacolone).
6. Solid state synthesis of benzilic acid from benzil.
7. Benzoin condensation using thiamine hydrochloride as a catalyst instead of potassium
cyanide.
8. Green multicomponent synthesis (three component coupling).
9. Base catalysed aldol condensation (synthesis of dibenzal propanone from
benzaldehyde and acetone).
10. Bromination of trans-stilbene using bromide/bromate mixture.
11. Preparation and characterization of gold nanoparticles using tea leaves.
12. Extraction of D-limonene from orange peel using liquid carbon dioxide.
13. Electrophilic aromatic substitution reaction (nitration of salicylic acid).
14. Green radical coupling reaction.

Reference Books

 Anastas, P.T & Warner, J.C. Green Chemistry: Theory and Practice, Oxford
 University Press (1998). 
 Kirchoff, M. & Ryan, M.A. Greener approaches to undergraduate chemistry
 experiment. American Chemical Society, Washington DC (2002). 
 Ryan, M.A. Introduction to Green Chemistry, Tinnesand; (Ed), American Chemical
Society, Washington DC (2002). 
 Sharma, R.K.; Sidhwani, I.T. & Chaudhari, M.K. I.K. Green Chemistry Experiment:
A monograph International Publishing House Pvt Ltd. New Delhi. Bangalore CISBN
978-93-81141-55-7 (2013). 
  Cann, M.C. & Connelly, M. E. Real world cases in Green Chemistry, American
 Chemical Society (2008). 
 Cann, M. C. & Thomas, P. Real world cases in Green Chemistry, American
Chemical Society (2008). 
 Lancaster, M. Green Chemistry: An Introductory Text RSC Publishing, 2nd Edition,
 2010. 
 Pavia, D.L., Lampman, G.M., Kriz, G.S. & Engel, R.G. Introduction to Organic
Laboratory Techniques: A Microscale and Macro Scale Approach, W.B.Saunders,
1995. 
9. Finar, I. L. Organic Chemistry (Volume 1), Dorling Kindersley (India) Pvt. Ltd. (Pearson
Education).

SEC T2 – ANALYTICAL CLINICAL BIOCHEMISTRY

(Credits: 2 Lectures:30)
Review of Concepts from Core Course
Agents for transfer of electrons in biological redox systems: NAD,FAD.
Carbohydrates: Biological importance of carbohydrates, Metabolism, Cellular currency of energy
(ATP), Calorific value of food, standard caloric content of food types. Glycolysis, Alcoholic and
Lactic acid fermentations, Krebs cycle.
Isolation and characterization of polysachharides.
Proteins: Classification, biological importance; Primary and secondary and tertiary structures of
proteins: α-helix and β- pleated sheets, Isolation, characterization, denaturation of proteins.
Enzymes: Nomenclature, Characteristics (mention of Ribozymes), and Classification; Active site,
Mechanism of enzyme action, Stereospecificity of enzymes, Coenzymes and cofactors, Enzyme
inhibitors, Introduction to Biocatalysis: Importance in “Green Chemistry” and Chemical Industry.
Lipids: Classification. Biological importance of triglycerides and phosphoglycerides and
cholesterol; Lipid membrane, Liposomes and their biological functions and underlying
applications.
Lipoproteins: Properties, functions and biochemical functions of steroid hormones. Biochemistry
of peptide hormones.
Structure of DNA (Watson-Crick model) and RNA, Genetic Code, Biological roles of DNA and
RNA: Replication, Transcription and Translation, Introduction to Gene therapy.
Enzymes: Nomenclature, classification, effect of pH, temperature on enzyme activity, enzyme
inhibition.
Biochemistry of disease: A diagnostic approach by blood/ urine analysis.
Blood: Composition and functions of blood, blood coagulation. Blood collection and preservation
of samples. Anaemia, Regulation, estimation and interpretation of data for blood sugar, urea,
creatinine, cholesterol and bilirubin.
Urine: Collection and preservation of samples. Formation of urine. Composition and estimation
of constituents of normal and pathological urine.
Hands On Practical
Identification and estimation of the following:
1. Carbohydrates – qualitative and quantitative.
2. Lipids – qualitative.
3. Determination of the iodine number of oil.
4. Determination of the saponification number of oil.
5. Determination of cholesterol using Liebermann- Burchard reaction.
6. Proteins – qualitative.
7. Isolation of protein.
8. Determination of protein by the Biuret reaction.
9. Determination of nucleic acids
Reference Books

1. Cooper, T.G. Tool of Biochemistry. Wiley-Blackwell (1977).

2. Wilson, K. & Walker, J. Practical Biochemistry. Cambridge University Press (2009).
3. Varley, H., Gowenlock, A.H & Bell, M.: Practical Clinical Biochemistry, Heinemann, London
(1980).
4. Devlin, T.M., Textbook of Biochemistry with Clinical Correlations, John Wiley & Sons, 2010.
5. Berg, J.M., Tymoczko, J.L. & Stryer, L. Biochemistry, W.H. Freeman, 2002.
6. Talwar, G.P. & Srivastava, M. Textbook of Biochemistry and Human Biology, 3rd Ed. PHI
Learning.
7. Nelson, D.L. & Cox, M.M. Lehninger Principles of Biochemistry, W.H. Freeman, 2013.
8. O. Mikes, R.A. Chalmers: Laboratory Handbook of Chromatographic Methods, D. Van
Nostrand & Co., 1961.

SEC T3 – PHARMACEUTICALS CHEMISTRY

(Credits: 2 Lectures: 30)
Drugs & Pharmaceuticals
Drug discovery, design and development; Basic Retrosynthetic approach. Synthesis of the
representative drugs of the following classes: analgesics agents, antipyretic agents, anti-
inflammatory agents (Aspirin, paracetamol, lbuprofen); antibiotics (Chloramphenicol);
antibacterial and antifungal agents (Sulphonamides; Sulphanethoxazol, Sulphacetamide,
Trimethoprim); antiviral agents (Acyclovir), Central Nervous System agents (Phenobarbital,
Diazepam),Cardiovascular (Glyceryl trinitrate), antilaprosy (Dapsone), HIV-AIDS related drugs
(AZT- Zidovudine).
Fermentation
Aerobic and anaerobic fermentation. Production of (i) Ethyl alcohol and citric acid, (ii)
Antibiotics; Penicillin, Cephalosporin, Chloromycetin and Streptomycin, (iii) Lysine, Glutamic
acid, Vitamin B2, Vitamin B12 and Vitamin C.
Hands On Practical
1. Preparation of Aspirin and its analysis.
2. Preparation of magnesium bisilicate (Antacid).
Reference Books
1. Patrick, G. L. Introduction to Medicinal Chemistry, Oxford University Press, UK, 2013.
2. Singh, H. & Kapoor, V.K. Medicinal and Pharmaceutical Chemistry, Vallabh Prakashan,
Pitampura, New Delhi, 2012.
3. Foye, W.O., Lemke, T.L. & William, D.A.: Principles of Medicinal Chemistry, 4th ed., B. .I.
Waverly Pvt. Ltd. New Delhi.